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Also known as: Isoquercetin, 482-35-9, Hirsutrin, 3-glucosylquercetin, Quercetin 3-o-glucopyranoside, Quercetin 3-glucoside

Molecular Formula

C₂₁H₂₀O₁₂

Molecular Weight

464.4 g/mol

InChI Key

OVSQVDMCBVZWGM-QSOFNFLRSA-N

FDA UNII

6HN2PC637T

Isoquercetin is an orally bioavailable, glucoside derivative of the flavonoid quercetin and protein disulfide isomerase (PDI) inhibitor, with antioxidant and potential antithrombotic activity. As an antioxidant, isoquercetin scavenges free radicals and inhibits oxidative damage to cells. As a PDI inhibitor, this agent blocks PDI-mediated platelet activation, and fibrin generation, which prevents thrombus formation after vascular injury. In addition, isoquercetin is an alpha-glucosidase inhibitor. PDI, an oxidoreductase secreted by activated endothelial cells and platelets, plays a key role in the initiation of the coagulation cascade. Cancer, in addition to other thrombotic disorders, increases the risk of thrombus formation.

1 2D Structure

Isoquercitrin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

2.1.2 InChI

InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1

2.1.3 InChI Key

OVSQVDMCBVZWGM-QSOFNFLRSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O

2.1.5 Isomeric SMILES

C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

6HN2PC637T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(3,4-dihydroxyphenyl)-3-(beta-d-glucofuranosyloxy)-5,7-dihydroxy-4h-1-benzopyran-4-one

2. 4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-d-glucofuranosyloxy)-5,7-dihydroxy

3. Flavone, 3,3',4',5,7-pentahydroxy-, 3-beta-d-glucofuranoside

4. Isoquercetin

5. Isoquercitin

6. Isoquercitroside

7. Isotrifoliin

8. Quercetin 3-(beta-d-glucofuranoside)

9. Quercetin 3-o-beta-d-glucofuranoside

10. Quercetin-3-glucoside

11. Quercetin-3-o-beta-glucoside

12. Quercetin-3-o-glucoside

13. Trifoliin

14. Trifoliin A

2.3.2 Depositor-Supplied Synonyms

1. Isoquercetin

2. 482-35-9

3. Hirsutrin

4. 3-glucosylquercetin

5. Quercetin 3-o-glucopyranoside

6. Quercetin 3-glucoside

7. Isotrifoliin

8. Quercetin 3-d-glucoside

9. Quercetin 3-o-glucoside

10. Quercetol 3-monoglucoside

11. Glucosyl 3-quercetin

12. Contigoside B

13. Quercetol 3-glucoside

14. Quercetin-3-o-glucopyranoside

15. Quercetin-3-o-glucoside

16. Quercetin 3-monoglucoside

17. Quercetin 3-beta-glucoside

18. Quercetin-3-glucoside

19. Quercetin 3-beta-o-glucoside

20. Quercetin Glucoside

21. Quercetin-3-glucose

22. Ronacare Isoquercetin

23. Glucosyl-3-quercetin

24. Isoquercetin, (-)-

25. 3-beta-d-glucosylquercetin

26. Quercetin 3.beta.-glucoside

27. 6hn2pc637t

28. Chembl250450

29. Chebi:68352

30. 3,3',4',5,7-pentahydroxyflavone 3-beta-glucoside

31. Quercetin 3-o-.beta.-d-glucopyranoside

32. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-4h-chromen-4-one

33. Quercetin 3-beta-d-glucoside

34. Quercetin 3-o-beta-d-glucopyranoside

35. Nsc-115918

36. Nsc-407304

37. Quercetin 3-o-beta-d-glucoside

38. 2-(3,4-dihidroxyphenyl)-3-(beta-d-glucofuranosyloxy)-5,7-dihydroxy-4h-1-benzopyran-4-one

39. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one

40. Smr000466391

41. Nsc 115918

42. Brn 0100989

43. Hydroside

44. Unii-6hn2pc637t

45. Ccris 9340

46. Isoquercitrin (6)

47. Mfcd00017746

48. Acacia

49. 3-glucoside Isoquercitrin

50. Quercetin 3--d-glucoside

51. Isoquercitrin [mi]

52. Isoquercetin [inci]

53. Quercetin 3-glucopyranoside

54. Quercetin 3-ss-d-glucoside

55. 4-18-00-03493 (beilstein Handbook Reference)

56. Mls000759532

57. Mls001424096

58. Q 5

59. Schembl181306

60. Acon1_002134

61. Cid_5280804

62. Cid_5378597

63. Quercetin 3- Beta -d-glucoside

64. Quercetin 3-o--d-glucofuranoside

65. Bdbm153265

66. Hms2051b17

67. Quercetin-3-o-beta-glucopyranoside

68. Hy-n1445

69. Zinc4096845

70. Bdbm50241354

71. Pdsp1_001363

72. Pdsp2_001347

73. S3842

74. Akos015896729

75. Ccg-100967

76. Db12665

77. Nc00217

78. Quercetin-3-o-beta-d-galactopyranoside

79. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-3-yl Beta-d-glucopyranoside

80. 4h-1-benzopyran-4-one, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-3-(beta-d-glucopyranosyloxy)-

81. 4h-1-benzopyran-4-one,2-(3,4-dihydroxyphenyl)-3-(b-d-glucopyranosyloxy)-5,7-dihydroxy-

82. Quercetin -3-o-beta-d-galactopyranoside

83. As-35335

84. Quercetin-3-o-.beta.-d-glucoside

85. Quercetin 3-glucoside, Analytical Standard

86. Quercetin-3-.beta.-glucopyranoside

87. 3-o-.beta.-d-glucopyranosylquercetin

88. Cs-0016884

89. C05623

90. Quercetin 3-o-glucopyranoside [who-dd]

91. Ab00639942-06

92. Quercetin 3-beta-d-glucoside, >=90% (hplc)

93. 3,3',4',5,7-pentahydroxyflavone 3-a-glucoside

94. A871939

95. 3-glucopyranosyloxy-3',4',5,7-tetrahydroxyflavone

96. Q-100268

97. Q6086296

98. Brd-k73991644-001-01-7

99. 3,3'',4'',5,7-pentahydroxyflavone-3-beta-o-glucoside

100. Isoquercitrin, Primary Pharmaceutical Reference Standard

101. Quercetin 3-o-glucoside (constituent Of Ginkgo) [dsc]

102. 3',4',5,7-tetrahydroxyflavone-3-.beta.-d-glucopyranoside

103. 2-(3,4-dihydroxyphenyl)-3-(beta-d-glucopyranosyloxy)-5,7-dihydroxy-4h-1-benzopyran-4-one

104. 2-hydroxy-4-(3,5,7-trihydroxy-4-oxo-4h-chromen-2-yl)phenyl B-d-glucopyranoside

105. 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-4-one

106. 2-(3,4-dihydroxyphenyl)-3-(b-d-glucopyranosyloxy)-5,7-dihydroxy-4h-1-benzopyran-4-one, 9ci

107. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one

108. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one

109. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one

110. 4h-1-benzopyran-4-one, 2- (3,4-dihydroxyphenyl)-3- (ss-d-glucofuranosyloxy)-5,7-dihydroxy-

111. 4h-1-benzopyran-4-one, 2-(3,4-dihydroxy-phenyl)-3-(.beta.-d-glucofuranosyloxy)-5,7-dihydroxy-

112. 4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(.beta.-d-glucopyranosyloxy)-5,7-dihydroxy-

113. Hw2

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₀O₁₂
Molecular Weight	464.4 g/mol
XLogP3	0.4
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	4
Exact Mass	464.09547607 g/mol
Monoisotopic Mass	464.09547607 g/mol
Topological Polar Surface Area	207 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	758
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 FDA Pharmacological Classification

4.1.1 Pharmacological Classes

Cell-mediated Immunity [PE]; Increased Histamine Release [PE]; Increased IgG Production [PE]; Non-Standardized Plant Allergenic Extract [EPC]; Plant Proteins [CS]; Allergens [CS]

NDC API